Originally the film was a more special-effects oriented, blockbuster-type movie and was turned down by Al Pacino five times. But when Taylor Hackford went through a few script re-writes he offered it to Pacino again. Pacino liked it, but didn't think he could portray Milton properly, and suggested Sean Connery or Robert Redford instead.
Each time Mary Ann (Charlize Theron) tries a different color of green on the apartment walls, only to be discouraged by her "friend" Jackie (Tamara Tunie), Jackie is wearing some article of clothing or jewelry that is the exact same shade of green.
The outdoor patio in John Milton's office actually was on the 50th floor of a New York building. The actual stage was 8ft away from the edge of the building. Thus what one would imagine is a bluescreen shot is actually real.
The boxing match that Lomax and Milton attend was not a staged bout, but in fact a legitimate world championship boxing match. The bout occurred on October 4, 1996, at Madison Square Garden in New York City. Roy Jones Jr., IBF super-middleweight champion, squared off against top contender Bryant Brannon. Jones knocked out Brannon during the second round of the bout.
The character of John Milton is named for John Milton, the author of "Paradise Lost," the classic epic poem about man's fall from God's grace. When Lomax is in Milton's office at the end of the film, he says "Better to reign in Hell than serve in Heaven," from Book I Line 263 of the same work.
Sculptor Frederick Hart and the Episcopal National Cathedral in Washington, DC, sued Warner Brothers over a sculpture that appears in the film and closely resembles Hart's "Ex Nihilo", which is situated above Milton's desk in his apartment. Warner Bros. agreed to edit the scenes for future releases. Some videos of the film had already been made, so they attached stickers to them, prior to sale, stating that there was no relation between the sculpture in the film and Hart's work.
Lomax and Milton run into Don King at the bout. King was in attendance that night because one of the fighters he promoted at the time, Oba Carr, fought on the undercard of the Roy Jones Jr.-Bryant Brannon bout. Carr lost a 12-round decision to WBA welterweight champion Ike Quartey.
At the end of the movie Keanu Reeves appears moving by an totally empty New York City's Fifth Avenue, without cars or people. This scene was victim of a certain polemic due to Open Your Eyes (1997), where its main actor, Eduardo Noriega, appears in a too empty Madrid's Gran Vía, creating a doubt about which of the two scenes was copied (or plagiarized) of the other.
According to the director's commentary on the DVD, after they finished filming Daniel Oreskes's scene in which he coughs violently for several minutes, the entire cast and crew broke out into applause.